


The one where Gabe thought William was a girl.

by wankiero



Category: Cobra Starship, The Academy Is...
Genre: Crossdressing, M/M, back ally sex
Language: English
Status: Completed
Published: 2013-06-19
Updated: 2013-06-19
Packaged: 2017-12-15 11:30:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 5,100
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/849052
Author URL: https://archiveofourown.org/users/wankiero/pseuds/wankiero
Summary: <blockquote class="userstuff">
              <p>Gabe goes out looking to pick up a girl and ends up with something better.</p>
            </blockquote>





	1. The one where Gabe thought William was a girl.

Gabe Saporta was horny. Not just your normal horny, he was 'haven't had a fuck in 18 months, 3 weeks and a day' horny. Usually he'd just get over it with the help of his left hand and a subscription to numerous porn sites but that just wasn't enough. Gabe was never big on picking up random chicks at bars either, fucking them then giving them false pleasantries like 'I'll call you' or 'We should do this again sometime' all the while both of them knowing it was a load of shit. He also wasn't attracted to the idea of a long term deal. Relationships were complicated, stressful and over all not worth it. Relationships leave you with an apartment you can hardly pay for, a sense of betrayal and abandonment and maybe if you're really lucky a cat that sleeps, walks around like it owns the place and shits in your shoes, not that Gabe was speaking bitterly from experience of course. The way Gabe saw it he only had those two options so because obviously the latter was completely out of the question Gabe found himself out on the town on a Saturday night armed only with $30 and a condom.

The first bar Gabe went into was relatively dead, there were a few men leaning against the bar drinking away there sorrows like they'd find the answer to all their problems at the bottom of a whiskey glass. Gabe really didn't want to be around that sort of people so he moved on. The next bar he went into was packed, music pumping around the room and people shouting over it while they sway along with the beat. The atmosphere was really nice and Gabe settled in on one of the bar stools feeling up beat and positive. He ordered a drink and leaned against the bar looking around. There were a few nice looking girls but they were all obviously on a 'girls night out' and Gabe knew better than to try his luck. The only women who were paying any attention to him were middle aged women in tight dresses who kept calling him ‘fresh meat’. Gabe was flattered by the interest but women over the age of 40 who still dressed like they were 19 weren’t really his area.

It took Gabe until he was in his 6th bar to give up. He sat at the bar downing a glass of Jack Daniels and frowning at the feeling that he was right back where he started the evening, with the men drowning their sorrows in whiskey except this time Gabe was the poor soul. He'd gotten to the stage where he was feeling sorry for himself, he was a 25 year old guy who lived alone, worked in a shitty record shop and could hardly even afford this night out.

Gabe pushed the thoughts away, the night wasn't over yet and he still maybe still had a chance to get his end away. His eyes swept noncommittally around the room, not expecting to see anyone but then his eyes locked with big brown ones and he almost fell off his stool. The girl was chewing at her straw seductively, brown shoulder length hair falling perfectly around the frame of her face. Gabe let his eyes drop down over her body; Her red v-neck clung to her skinny frame in all the right places, her hip bones jutting out around the waist of her tight black skirt. Gabe swallowed, hard. This girl looked fucking amazing, so amazing that it didn't even faze Gabe that she was severely lacking in the breast area, Gabe had always been a boob sort of guy but there were always exception. He looked back up at the girls eyes and a smile tugged at the corner of his lips when he realised she was checking him out as well. Gabe took his opportunity and slipped off of the stool and went over, he leaned against the bar next to the girl and she ducked her head shyly ''Can I buy you a drink?'' Gabe asked smoothly, nodding at the empty glass in the girls hand. She nodded, her cheeks a rosy colour. ''Same again?'' Gabe asked, he'd seen her drinking what looked like a vodka and soda. The girl nodded again not saying a word

''Double vodka and soda please.'' Gabe asked the bar man then added ''And a pint of whatever you have on tap.'' The bartender nodded and started pouring their order. Gabe looked back at the girl, he could tell she was really shy so he decided to try and start the conversation ''So, I'm Gabe.'' He introduced himself and the girl smiled softly at him before looking at the barman who placed a drink in front of her. She put the straw back in her mouth and started to drink it. Gabe blinked at her and asked ''So..what's your name?'' The girl tucked her hair behind her ear and shrugged, Gabe frowned in confusion ''You don't know..?'' To that the girl shook her head, Gabe went to ask what she meant but was distracted by the way she was swirling her tongue around the end of the straw, looking at Gabe intently. Gabe swallowed hard and choked out ''Not a talker then?'' She shook her head and dropped her eyes down to Gabes crotch and started sucking on her straw. She then looked back up at Gabe with propositioning eyes and Gabe blinked at her again for a long moment before asking in a breathless voice ''Do you want to get out of here?'' She didn't hesitate before pulling the straw out of her glass, downing her drink and nodding. Gabe was stunned for a moment before he downed half his drink as well, placed a $10 on the bar, grabbed the girls hand and lead her out of the bar.

Once outside the girl dragged Gabe down the nearest ally, that was an all new low for Gabe but he couldn't bring himself to care about how dirty the ally must be when a girl that hot was the one dragging him down it. As soon as they turned the corner, out of the sight of everyone she dropped to her knees and started working at Gabes belt. Gabes mouth fell open ''You..you don’t have to-'' He cut himself off with a gasp as his cock was released into the cold night air. It wasn't out for long though because the girl wrapped her lips around him and swallowed him down into the heat of her mouth. Gabe dropped his head back against the brick wall and shuddered ''Oh, fuck, darling your mouth..'' he purred and petted the back of her hair as she bobbed her head up and down, smiling slightly around his cock as she did so. Gabe looked back down at her and their eyes locked, her pupils were blown and she was taking every inch of Gabes cock into her mouth hungrily. Gabe could see her skirt was riding far up her thighs to reveal sides of red lace panties, he groaned at the sight and the hot tight sensation of the girls mouth around his cock.

He came a lot sooner than he wanted but he couldn't help it, everything was too much and too good all at once. Gabe tugged lightly on the back of the girls head as warning that he was about to come, she didn't pull off though, she just moaned around Gabes cock and sucked harder, her tongue doing things that was sending Gabe insane. Once Gabe had come he leant all his weight against the wall, scared that if he didn’t he was going to collapse. The girl looked up at him through her lashes, hair fallen in her face and her tongue still connected to Gabes flush cock by a strand of spit, her lips bright red and plump. Gabe could hands down say that was the hottest thing he'd ever seen in his life. The girl fastened him back up before getting to her feet, her cheeks bright red and her hair a mess. Gabe stared at her in disbelief for a moment before wrapping his arms around her skinny waist and pulling her against him. She looked worried and gnawed at her bottom lip. ''Are you alright?'' Gabe asked in concern, hoping her hadn't upset her. She nodded and pulled her skirt down from where it had ridden up. Gabe looked down and turned them around so she was pressed against the wall, she gasped and fisted her hands into Gabes shirt, her hips trying to press forward against Gabes. He smiled and started hungrily kissing her neck ''You should tell me your name.'' He mumbled against her neck as he slowly ran his hand up her skirt.

His hand was millimetres away from reaching it's destination when the girl gasped out ''William.'' Gabes hand was greeted by a hot, rock hard cock. His jolted his hand away like he'd been burnt, he almost fell backwards but she-no he-William caught him ''Shit, I'm sorry.'' William apologized and pulled his skirt down again from where Gabe had made it ride up again.

Gabe just started at William with wide eyes ''I...thought you were a chick.'' Gabe said dumbly.

''Uh..yeah, I do give that impression..'' William tucked a piece of hair behind his ear ''You can run away screaming now.''.

He knew that would be a good idea, just turn away and leave and forget about the whole gay ordeal but Gabe was glued to the spot ''You're wearing a skirt.'' Gabe pointed out obviously.

''Yeah..I know. I look good in a skirt.''

Gabes mouth was still hung open and he eyed William up and down again, he was still just as attractive, even though he most certainly had a cock. Hell, Gabe could see his hard on through the fabric of Williams skirt ''Yeah, you do.'' he swallowed.

William chewed on his lip ''Suppose you returning the favour is out of the question?''

Gabe suddenly felt really rude, he'd just gotten one of the hottest blow jobs in his life and he wasn't going to return the favour. He swallowed hard, fully intending to say 'I'm not gay' but what came out was ''I don't know what to do.''

Williams still red lips quirked up into a grin, he reached forward and wrapped his long fingers around Gabes hand and slowly started to run it up his thigh ''Here,'' William said, and bit his lip, watching Gabes reaction ''I'll show you.'' Gabe nodded silently, he really should be pulling away but he couldn't, he was curious. He didn't know if he should put it down to the alcohol or his lack of sex but it didn't really matter at the moment because his hand was up a guy’s skirt, inches from his cock. William slowly pressed Gabe's hand against the bulge in his panties and gasped against the feeling of Gabes hot palm. Gabe bit his lip, the feeling of the soft panties against his hand and the rock hard cock that just seemed out of place was more arousing than it should have been.

William held Gabes hand flat against his cock and started rocking into his touch. Gabe watched in awe at the sight of his hand up Williams skirt, his legs apart and making quiet needy noises in the back of his throat. Gabe squeezed Williams cock through the fabric experimentally and William gasped and let go of Gabes hand, Gabe kept it under his skirt, rubbing in the same way William had been making him do. William fisted his hands into Gabes shirt and whimpered. Gabe bit his lip before dipping his fingers under Williams panties and wrapping his fingers around Williams cock. He had no fucking idea what had come over him but he didn't care.

The feeling of a cock in his hand that wasn't his own was weird to Gabe but not unpleasant. He started pumping his hand up and down Williams cock, it was all backwards to how Gabe did to himself but he soon got the hang of it. William moaned and pressed himself into Gabes hand and clung to him.

William dropped his head back against the cold stone wall and Gabe looked up at his face and down his throat, there was an obvious lump where his adams apple was and Gabe leant forward to kiss it gently, his hand picking up pace on Williams cock. William whined and bucked his hips forward into Gabes hand. Gabe eyed William up, his mouth slightly open, he was completely in awe at how attractive this guy was, as a girl he was breath taking and that didn’t change once Gabe found out he had a dick.

‘’You’re fucking gorgeous.’’ Gabe hadn’t even registered he’d said that until a few seconds after the words left his mouth. William blushed and closed his eyes.

‘’Not too bad yourself.’’ William laughed breathlessly.

Gabes arm was starting to hurt and he really wanted to get William off so he tightened his fist around Williams cock and pumped quicker. He wished he could record the sounds William was making because he’d never need to watch porn again. William whimpered and buried his face into Gabes neck ‘’So close.’’

When William came Gabe wrapped his arm tightly around Williams waist and held him close to his body to keep him up. Williams come went all over his skirt and panties and Gabe held back a moan at how hot the whole image was, Williams come dripping in his red panties and down Gabes hand.

After William came down from his orgasm he sorted himself out and wiped down his skirt. He looked up at Gabe who was looking into thin air. ‘’Are you having a homosexual crisis?’’ William laughed lightly.

Gabe snapped out of it and looked at William ‘’Actually, yeah. Little bit.’’ Gabe straightened his shirt and put his hands in his pockets ‘’I have a kink for guys in skirts apparently. Learn something new every day.’’

William smirked ‘’I’d be lying if I said you were the first person I’d converted.’’

“You do this a lot then?’’ Gabe asked.

“only a few times a month.’’

“Damn, I thought I was special.” Gabe teased, surprised at how comfortable the conversation was getting already.

William laughed “Well, I suppose I’ve never gotten someone’s number after a hook up, so that makes you a little bit special.”

“What makes you so sure you’re getting my number?”

William raised an eyebrow and after a few moments Gabe laughed and pulled out his phone.


	2. The one where Gabe knew William wasn't a girl this time.

**Summary for the Chapter:**

> He'd never really experimented with his sexuality when he was younger, he'd never felt the need to. That got Gabe thinking; why does the experimenting stop when you're no longer a teenager? That was all the convincing he needed to do for him to pick up the phone and text William.

The next couple of days were seriously weird for Gabe. He couldn't stop thinking about William. His feelings wavered between complete panic to so turned on he thought his balls were going to explode. It was fucking weird. William was a quite firmly established male and Gabe was (as far as he knew) a heterosexual male. But the more Gabe thought about it the more he started to wonder. He'd only ever touched two dicks in his life; His own and Williams. So, he'd enjoyed 100% of the cocks he'd touched, where as he's only really liked about 70% of the vagina's he'd touched so statistically he was pretty fucking gay.  
He'd never really experimented with his sexuality when he was younger, he'd never felt the need to. That got Gabe thinking; why does the experimenting stop when you stop being a teenager? That was all the convincing he needed to do for him to pick up the phone and text William.

'Hey its gabe. from last week?' He sent, chewing the inside of his cheek nervously.

'Gabe? nope doesnt ring any bells'

Gabe's heart sunk into his stomach 'from the alley..?'

'i know dude i was kidding. how's it goin'?'

Gabe let out a sigh of relief and sunk down in his bed. They text back and forth for most of the day, nothing too heavy, just some joking around small talk, Gabe had been stressed out so much about texting William that he'd forgotten how easy he was to talk to and how well they hit it off the week before.

Eventually things started heading in a different direction from the friendly banter after Gabe made a joke about Williams skirt.  
'its not the only one i have'

'oh? you should show me your others sometime' Gabe replied, getting nervous again.

'mhh i might do that.i think you'd like them better pushed up over my ass though.' Gabe gulped at the mental image of William on his hand sand knees in front of Gabe as he slid the skirt up over his ass to reveal panties like William had worn the other night.

'oh god yeah i do.'

'im free wednesday'

Gabes eyes widened and he nodded dumbly even though William couldn't see him 'Me too'

the next text Gabe received was an address and he quickly saved it to his phone and text back 'see you then'

 

When Wednesday came Gabe debated not going, changing his number and maybe even moving to Alaska. He was so unbelievably nervous, his bitten down his nails and was surprised he hadn't worked a path in his carpet from how much he'd been pacing. He didn't want to go, he was going to probably freak out as soon as he saw Williams dick and end up running away or something equally as embarrassing. But at the same time he couldn't fucking wait to go, he couldn't wait to be behind closed doors with William and maybe even fuck him, play out all the fantasies he'd had since he'd met William. That feeling was soon replaced by 'oh my god I want to fuck a dude.'. It was terribly conflicting and Gabe was confused, panicked, and painfully turned on.

Despite all this Gabe still found himself stood outside Williams front door quarter of an hour before he was even supposed to be there. From inside Gabe heard footsteps approaching and the faint clacking of heals and he swallowed nervously.

William opened the door and smirked, leaning against the door frame. He was wearing a tight red skirt that Gabe was sure probably only just covered his ass, stockings with suspenders that disappeared under the skirt. He wasn't even wearing a shirt and Gabe's eyes raked over the smooth paleness of his chest and stomach, the v's of his hips deep and his hip bones sharp and Gabe wanted to feel them against his palm. He stood there for a long time just gaping at William who giggled and said ''You coming in or what?''

Gabe nodded sheepishly and stepped into the house, shuffling passed William who wasn't budging from the door way. William smirked and closed the door behind him and quirked an eyebrow at Gabe ''How's your homosexual crisis coming?''

''Not very good actually.'' Gabe laughed weakly.

''Mhh? Why's that?'' William purred, draping his arms over Gabe's shoulders and pressing himself up against him.

''Um.'' Gabe choked and he held Williams hips, for filling his desire to do so before ''Wanting to fuck guys is still pretty new.''

''Oh? Met another guy you want to fuck as well?'' William asked, tilted his head to the side.

''Well..no. Fucking a guy then.''

''Aw, I'm definitely special then.'' William smiled, his fingers playing lazily with the hair at the nape of Gabe's neck. He bit his lip before leaning in, his lips ghosting over Gabe's ear before whispering ''How about we go upstairs and I show you what you've been missing.''

Gabe let out a pathetic noise that he'd be embarrassed of if he could even concentrate enough on anything but William to care. He nodded immediately and William grinned widely before stepping back and taking one of Gabe's hands and leading him up the stairs. His hips swung with every step he took up and Gabe could see up his skirt, bright blue panties visible and he made another quiet noise which William giggled at.

Gabe couldn't even stop himself wrapping his arms around Williams waist as soon as they were at the top of the stairs and pushing him against the wall. William gasped and pushed his ass back against Gabe's crotch and Gabe let out a shuddered breath, digging his nails into Williams hips and kissing the side of his neck. ''Someones eager.'' William giggled and Gabe pushed forward, pressing William up against the wall from his chest to his crotch, hoping that counted as an answer.

William smirked and dropped his head back against Gabe's shoulder and Gabe instantly went to kissing the newly exposed skin on Williams neck. William reached up and fisted his hand into the back of Gabe's hair and Gabe reached up to hold Williams chest so he was still held firmly against Gabe's body. He then kissed up Williams neck and jaw and William turned himself around and crushed their lips together, pushing Gabe back against the stairs banister. Gabe kissed back, reaching down to pull Williams skirt up so he could squeeze his ass, the thin material of his panties soft against Gabes hands.

William gasped against Gabe's lips ''Bedroom?'' He asked breathlessly and Gabe nodded, pushing himself away from the banister and walking William backwards into his bedroom.

All Gabe's panic and worry having slipped away for now the moment he got his hands on William. Gabe was then swung around by William, pushed down onto the bed and then climbed on top of. William straddled Gabe's waist and ran his hands up Gabe's chest then back down before slowly rocking his hips down against Gabe's. Gabe stared up at William and ran his hands up his smooth thighs, his fingers dipping under his skirt then back down again, his thumbs hooked around the suspender strap briefly, pulling up and letting them snap back down against Williams thighs.

''Gunna tell me what you want?'' William asked coyly as he rolled his hips down on Gabe's, his hands idly popping open the buttons of Gabe's shirt one by one.

Gabe struggled to form what he wanted into words so it took him a minute, a minute where he watched as William unbuttoned his pants and started pulling them off. Eventually he managed ''You, on your hands and knees.''

''Excellent choice.'' William smirked and pulled the rest of Gabe's clothes off. Gabe watched as William crawled onto the bed on his hands and knees, his ass in the air and panties on full display, he then leaned forward to get a condom and a bottle of lube from his drawer and looked over his shoulder at Gabe ''Don't need to get me ready much, did that before you got here.'' Gabe's jaw dropped open at the mental image of William spread out on his bed, fingering himself open for Gabe's cock.

''Oh god.'' Gabe breathed and got on his knees behind William, pressing his cock against the thin material on his panties and digging his fingers into Williams hips. William pushed back against Gabe's cock, sending him the hint to hurry up. Gabe decided to take his time and leaned down, kissing between Williams shoulder blades then down the curve of his spine making William shiver and drop his head onto the pillow. Gabe ran his hands up Williams sides then slowly dragged his hands back down, nails digging in ever so slightly, not enough to hurt but enough for William to feel it.

William whimpered ''C'mon Gabe, want your cock,'' He said into the pillow and Gabe's breath hitched in his throat and that's all the encouragement he needed and reached over for the condom.

Once it was on and Gabe was all lubed up he hooked his fingers into the panties and pulled them down over Williams ass and half way down his thighs, not wanting him to take them off completely. Gabe took in a deep breath and bit his lip and he rubbed his hands up over Williams ass and pushed his skirt up just enough to be out of the way. William whined at Gabes slow pace and Gabe couldn't keep it up anymore and positioned himself before slowly pushing himself inside of William, his hands hooked around the front of Williams thighs.

''Fuck,'' Gabe breathed ''You feel so good.'' He dropped his head down onto Williams back as he pushed himself all the way into William. William moaned and pushed himself back on Gabe's cock, taking as much as he could.

Gabe had never done this before, not even with a girl, it was so tight and hot and Gabe couldn't believe he hadn't tried it before. He gripped Williams hips tightly and started to pull out a little bit just so he could thrust back in which caused William to make these noises that Gabe knew he was probably going to be hearing for weeks after this and jerking off in the shower to. ''Faster,'' William whimpered ''C'mon, I wont break.''

Gabe nodded and bit down hard on his bottom lip and picked up the pace. His thighs already felt like they were going to give way but Gabe stuck it out, there was no way he wanted to move from the position. He sat up and held onto the waistband of Williams skirt and pulled out almost all the way before pulling William back down on his dick by his skirt. William moaned loudly and let Gabe do it again while William bit down on a pillow and fisted into the sheets.

Gabe had never felt this good during sex, everything just felt so amazing and Gabe hated himself for how close he was already. He really didn't want this to end yet, but everything felt too good and it was hard to last very long. Before he could over think it Gabe reached in front of William and slipped his hand up his skirt and wrapped his hand around Williams hard cock. William took in a sharp breath, clearly not expecting Gabe to do that and that made Gabe smirk. He started to jack William off in time with his own thrusts and William moaned approvingly and reached down as well, wrapping his own hand around Gabe's and squeezed so Gabe knew how tightly to grip him, he was so thankful for the help.

''So close,'' William whimpered, sounding desperate and Gabe nodded, pushing in harder and trying to move his hand faster on William cock, wanting him to feel amazing when he came.

William actually came first, spilling into Gabe's hand and down the inside of his thigh, moaning Gabe's name needily and encouraging Gabe to carry on fucking him. Gabe did and moved his hands back to Williams hips, pulling him back into Gabe's thrusts. William let Gabe just use him like that to fuck into and fucking loved it, Gabe knew this from how much William was telling him as he did so.

When Gabe came he was surprised he didn't black out. He fell forward onto Williams back, resting his forehead between his shoulder blades and moaned shakily as he came harder than he had probably in his life.

Gabe slowly pulled out of William and rolled onto his back, his chest rising and falling rapidly as he tried to catch his breath. William looked over at him and giggled breathlessly before placing an open mouth kiss on his neck and reaching down to pull Gabes condom off for him and throw it in the bin. Gabe looked down and smiled weakly ''Thanks.'' He mumbled, his voice hoarse.

William lay onto his back next to Gabe, their shoulders pressed against one another as they both caught their breath and calmed down. Gabe lolled his head to the side to look at William and laughed ''Okay, yeah. I've definitely been missing out.''

They lay in bed for another half an hour, naked and still covered in sweat, William kicked his panties off but kept on the suspenders and skirt the whole time. William rolled over and propped his head up on his hand ''You hungry?'' He asked and Gabe nodded enthusiastically, he'd been too nervous to eat all day. William smiled and got up out of bed ''I'm for a quick shower first.'' He said, picking up a towel ''Joining me?''

 

Showers where you came out feeling dirtier than you did going in were Gabe's fucking favorite kind of showers. So, he sat at the table in Williams kitchen with a big goofy grin on his face and his hair still damp and sticking to his head. William had stayed in the bedroom to dry his hair and when he came out he was wearing a shirt that was way too big for him and some pajama bottoms that were too long for his legs and Gabes smile grew even more, William was fucking adorable. That was kind of shocking for Gabe, he was used to just seeing William as really hot and he'd never even seen William in anything but a skirt and now he had he realised that William was actually really cute as well as insanely hot which maybe should have caused Gabe to have another sexual identity crisis but he was just going with it now, it was evidently more fun that way. William smiled at Gabe and padded into the kitchen ''What would you like to eat?''

They ended up sitting on the sofa watching Spongebob and eating pancakes and Gabe was so relaxed and couldn't stop smiling. William teased him about being smiley but Gabe just told him he was having a really fucking good day.

After they'd finished their pancakes and the episode of Spongebob they were watching finished William slung his leg over Gabe's waist and sat on his lap, straddling him and looking down at him innocently ''So are you going to leave later and then never call me again or are you planning on making this a regular thing?'' He asked, playing with the material of Gabe's shirt clearly nervous and that made Gabe's heart tighten in his chest. He thought about it for a moment and wrapped his arms around Williams skinny waist.

''Hmm, I wouldn't mind doing this again.'' He said nonchalantly like today hadn't been one of the best days he'd had in his life.

''Oh?''

''Or you know.. a few more times.''

''A few?''

''Or a lot.''

''Friday?''

''Definitely.''

**Author's Note:**

> Hey! So, this was my first fic on AO3 and I'm super nervous to post it. I hope you enjoyed!


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